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Acetonitrile → Ethyl (4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2,2-dioxide

HRID 249365
Notes
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Reaction equation

HRID 249365 reaction equation
[OH:1][C@@H:2]([C@H:8]([OH:25])[C:9](=[O:24])[NH:10][C@H:11]([C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([C@@]1(C([O-])=O)[C@@H](C(=O)N[C@H](C(=O)NCCC(C)C)CC(C)C)[O:31][S:30](=O)[O:29]1)C.C(#N)C.I([O-])(=O)(=O)=O.[Na+]>O.O.[Ru](Cl)(Cl)Cl.C(OCC)C.C(Cl)(Cl)(Cl)Cl>[CH3:14][CH:13]([CH3:15])[CH2:12][C@H:11]([NH:10][C:9]([C@H:8]1[O:25][S:30](=[O:31])(=[O:29])[O:1][C@@H:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:24])[C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 53688291Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionateHCID 86746871ethyl-(4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl) butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide

Product 1

HCID 54379098
Ethyl (4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2,2-dioxide

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

Following the same procedures as in Example 3, ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate (200 mg) was converted into ethyl-(4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl) butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide. Acetonitrile (3 ml) was added to the reaction solution (carbon tetrachloride; 3 ml) without isolating or purifying the product, and the resultant solution was stirred at room temperature. Subsequently, a solution prepared by dissolving sodium periodate (252 mg) and ruthenium trichloride hydrate (catalytic amount) in water (4.5 ml) was added, and the resultant solution was stirred at room temperature for 20 hours. Diethylether was added to the reaction solution, and the ether layer of the solution was sequentially washed with water, saturated sodium bicarbonate solution, and saturated sodium chloride solution. The resultant layer was dried with magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (a developing solvent; hexane:ethyl acetate=2:1) to obtain 117 mg of a target compound as a white powder. NMR data, IR data, and SIMS data of the compound were as follows.

Workup

  1. customwithout isolating
  2. custompurifying the product
  3. customSubsequently, a solution prepared
  4. additionwas added
  5. washthe ether layer of the solution was sequentially washed with water, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  6. dry with materialThe resultant layer was dried with magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a crude product
  9. customThis crude product was purified by silica gel column chromatography (a developing solvent

Sources & evidence

ORD record
ord-7bd6ca4d437f4ccf98a5ae64f83cdd36
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05214056

Reaction notes

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